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Highly Luminescent 4H-1,2,4-Triazole Derivatives: Synthesis, Molecular Structure and Photophysical Properties.

ABSTRACT: An alternative approach to the Suzuki cross-coupling reaction is used to synthesize a series of new luminophores based on 4-alkyl-4H-1,2,4-triazole cores conjugated via 1,4-phenylene linker to fused-bicyclic and tricyclic aromatic, or heteroaromatic arrangements. The described methodology allows one to conduct the coupling reaction with the use of commercially available boronic acids in the presence of conventional solvents or ionic liquids and produced excellent yields. It was found that the use of ultrasounds or microwaves significantly accelerates the reaction. The obtained compounds exhibited high luminescent properties and a large quantum yield of emitted photons. The X-ray molecular structures of three highly conjugated 4H-1,2,4-triazole representatives are also presented.

SUBMITTER: Olesiejuk M

PROVIDER: S-EPMC7764194 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Highly Luminescent 4<i>H</i>-1,2,4-Triazole Derivatives: Synthesis, Molecular Structure and Photophysical Properties.

Olesiejuk Monika M Kudelko Agnieszka A Świątkowski Marcin M

Materials (Basel, Switzerland) 20201210 24

An alternative approach to the Suzuki cross-coupling reaction is used to synthesize a series of new luminophores based on 4-alkyl-4<i>H</i>-1,2,4-triazole cores conjugated via 1,4-phenylene linker to fused-bicyclic and tricyclic aromatic, or heteroaromatic arrangements. The described methodology allows one to conduct the coupling reaction with the use of commercially available boronic acids in the presence of conventional solvents or ionic liquids and produced excellent yields. It was found that ...[more]

PMID: 33321753

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Novel Conjugated s-Tetrazine Derivatives Bearing a 4H-1,2,4-Triazole Scaffold: Synthesis and Luminescent Properties.

Project description:A series of new symmetrical s-tetrazine derivatives, coupled via a 1,4-phenylene linkage with a 4H-1,2,4-triazole ring, were obtained. The combination of these two rings in an extensively coupled system has significant potential applications, mainly in optoelectronics. The methodology used turned out to be useful regardless of the type of five-membered ring or the nature of the individual substituents. All the products were identified by spectroscopic methods, and the target compounds were tested for luminescent properties. This study showed that all the synthesized highly-conjugated triazoles exhibited luminescence; in particular, one derivative, 3,6-bis(4-(5-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazol-3-yl)phenyl)-1,2,4,5-tetrazine (13b), showed strong fluorescence emission and ahigh quantum yield close to 1.

| S-EPMC8779062 | biostudies-literature

Synthesis of 4-Alkyl-4H-1,2,4-triazole Derivatives by Suzuki Cross-coupling Reactions and Their Luminescence Properties.

Project description:New derivatives of 4-alkyl-3,5-diaryl-4H-1,2,4-triazole were synthesized utilizing the Suzuki cross-coupling reaction. The presented methodology comprises of the preparation of bromine-containing 4-alkyl-4H-1,2,4-triazoles and their coupling with different commercially available boronic acids in the presence of ionic liquids or in conventional solvents. The obtained compounds were tested for their luminescence properties.

| S-EPMC6384732 | biostudies-literature

Highly Emissive 9-Borafluorene Derivatives: Synthesis, Photophysical Properties and Device Fabrication.

Project description:A series of 9-borafluorene derivatives, functionalised with electron-donating groups, have been prepared. Some of these 9-borafluorene compounds exhibit strong yellowish emission in solution and in the solid state with relatively high quantum yields (up to 73.6 % for FMesB-Cz as a neat film). The results suggest that the highly twisted donor groups suppress charge transfer, but the intrinsic photophysical properties of the 9-borafluorene systems remain. The new compounds showed enhanced stability towards the atmosphere, and exhibited excellent thermal stability, revealing their potential for application in materials science. Organic light-emitting diode (OLED) devices were fabricated with two of the highly emissive compounds, and they exhibited strong yellow-greenish electroluminescence, with a maximum luminance intensity of >22 000 cd m-2 . These are the first two examples of 9-borafluorene derivatives being used as light-emitting materials in OLED devices, and they have enabled us to achieve a balance between maintaining their intrinsic properties while improving their stability.

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Synthesis of new, highly luminescent bis(2,2'-bithiophen-5-yl) substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole.

Project description:A new synthetic approach towards the preparation of functionalised, soluble, donor-acceptor (DA) alkylbithiophene derivatives of oxadiazole, thiadiazole and triazole is reported. Taking advantage of the Fiesselmann reaction, reactive bithiophene synthons having alkyl or alkoxy substituents at designated positions are prepared. Following a synthetic strategy, featuring the bottom-up approach, sequential structural elements are built, starting from a simple thiophene compound, until the target molecule is obtained, all in good yield. Supplementing the well established methods of oxadiazole and thiadiazole synthesis, efficient ring closure reaction affording a 4H-1,2,4-triazole unit is presented. All target ambipolar compounds display strong photoluminescence with measured quantum yields up to 0.59. Modification of the demonstrated synthetic routes may be exploited for the preparation of longer, specifically functionalised oligothiophenes, coupled to other heteroaromatic cores.

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4-Amino-3,5-dimethyl-4H-1,2,4-triazole.

Project description:In the title compound, C(4)H(8)N(4), inter-molecular N-H?N hydrogen bonds involving the amino groups and triazole N atoms form a two-dimensional sheet.

| S-EPMC2961470 | biostudies-literature

5-Amino-3-(4H-1,2,4-triazol-4-yl)-1H-1,2,4-triazole.

Project description:The asymmetric unit of the title compound, C(4)H(5)N(7), comprises two independent but virtually superimposable mol-ecules. Each mol-ecule is planar with the dihedral angles between the five-membered rings being 2.8?(3) and 2.1?(3)°. The crystal structure is formed by an extensive network of relatively strong N-H?N hydrogen-bond inter-actions. Individual mol-ecules are arranged into supra-molecular zigzag chains running parallel to [001] by way of the strongest N-H?N inter-actions. Adjacent chains are inter-connected by rather long (D?A distances range from ca 3.00 to 3.03?Å) but highly directional (inter-action angles above ca 173°) hydrogen bonds forming a supra-molecular layer in the bc plane.

| S-EPMC3435720 | biostudies-literature

Synthesis, antimycobacterial evaluation, and molecular docking study of 1,2,4-triazole derivatives.

Project description:Fifteen 1,2,4-triazole derivatives were synthesised in this study and their MIC values against Mycobacterium tuberculosis (Mtb) ranged from 2 to 32 μg/mL. Furthermore, their antimycobacterial activity was positively correlated with the KatG enzyme docking score. Among the 15 compounds, compound 4 showed the strongest bactericidal activity with an MIC of 2 μg/mL. The selectivity index of compound 4 is more than 10, indicating that the compound has low toxicity to animal cells and has the potential to become a drug. Molecular docking indicates that compound 4 can bind firmly to the Mtb KatG active site. The experimental results showed that compound 4 inhibited Mtb KatG and caused the accumulation of ROS in Mtb cells. We speculate that compound 4 causes the accumulation of ROS by inhibiting KatG, and ROS produces oxidative destruction, leading to the death of Mtb. This study provides a new idea for the development of novel anti-Mtb drugs.

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An Optimized Synthesis, Molecular Structure and Characterization of Benzylic Derivatives of 1,2,4-Triazin-3,5(2H,4H)-dione.

Project description:4-Benzyl-1,2,4-triazin-3,5(2H,4H)-dione (3-benzyl-6-azauracil, 2), and 2,4-dibenzyl-1,2,4-triazin-3,5(2H,4H)-dione (1,3-dibenzyl-6-azauracil, 3) were synthesized by the reaction of 1,2,4-triazin-3,5(2H,4H)-dione (6-azauracil, 1) with benzyl bromide and potassium carbonate in dry acetone via the 18-crown-6-ether catalysis. In these reaction methods, we developed more convenient and efficient methodologies to afford compounds 2 and 3 in good yields. These compounds were characterized by ¹H- and 13C-NMR, MS spectrum, IR spectroscopy and elemental analysis. The structure of 2 was verified by 2D-NMR measurements, including gHSQC and gHMBC measurements. A single-crystal X-ray diffraction experiment indicated that compound 3, with the molecular formula C17H15N₃O₂, crystallized from a CH₃OH/CH₂Cl₂ diffusion solvent system in a monoclinic space group P2₁/c with a = 13.7844(13), b = 8.5691(8), c = 13.0527(12) Å, β = 105.961(2)°, V = 1482.3(2) Å³, Z = 4, resulting in a density Dcalc of 1.314 g/cm³. The crystal structure of compound 3 is tightly stabilized by contact with five other molecules from the six short contacts formed by intermolecular C-O···H-Car, C-H···Car, and weakly π···π stacking interactions. The dihedral angle 31.90° is formed by the mean planes of the benzene rings of the N-2 and N-4 benzyl groups.

| S-EPMC6150235 | biostudies-literature

Synthesis and crystal structure of 3-(adamantan-1-yl)-4-(2-bromo-4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione.

Project description:In the title compound, C18H19BrFN3S, the 1,2,4-triazole ring is nearly planar with a maximum deviation of ?0.009?(3) and 0.009?(4)?Å, respectively, for the S-bound C atom and the N atom bonded to the bromofluorophenyl ring. The phenyl and triazole rings are almost perpendicular to each other, forming a dihedral angle of 89.5?(2)°. In the crystal, the molecules are linked by weak C—H??(phenyl) interactions, forming supramolecular chains extending along the c-axis direction. The crystal packing is further consolidated by intermolecular N—H?S hydrogen bonds and by weak C—H?S interactions, yielding double chains propagating along the a-axis direction. The crystal studied was refined as a racemic twin.

| S-EPMC7001835 | biostudies-literature

Poly[(?(3)-hydrogenphosphato)(4H-1,2,4-triazole-?N(1))zinc].

Project description:The asymmetric unit of the title compound, [Zn(HPO(4))(C(2)H(3)N(3))](n), contains one Zn(2+) cation, one (HPO(4))(2-) anion and a 1,2,4 triazole ligand. The Zn(2+) cation is coordinated in a quite regular tetra-hedral geometry by O atoms from three phosphate groups and a tertiary N atom from the triazole ring. Each phosphate anion is connected to three Zn(II) cations, leading to a series of corrugated organic-inorganic layers parallel to the ac plane. The overall structure involves stacking of complex hybrid organic-inorganic layers along the b axis. Cohesion in the crystal is ensured by an infinite three-dimensional network of N-H?O and O-H?O hydrogen bonds between the phosphate groups and the triazole ligands.

| S-EPMC3515161 | biostudies-literature

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